


An Alternative Route

by ahunmaster



Series: Office AU [56]
Category: Transformers - All Media Types
Genre: AU, Alternate Universe, Alternate Universe - Human, Alternate Universe - Modern Setting, Anal Sex, Explicit Sexual Content, F/M, Genderbending, Human, Sex, Sexual Content, Smut
Language: English
Status: Completed
Published: 2016-05-11
Updated: 2016-05-11
Packaged: 2018-06-07 20:31:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,459
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6822943
Author URL: https://archiveofourown.org/users/ahunmaster/pseuds/ahunmaster
Summary: <blockquote class="userstuff">
              <p>Cyclonus runs out of condoms, so Tailgate suggests something else.</p>
            </blockquote>





	An Alternative Route

Often the first time one does something is because of several reasons. Adrenaline, peer pressure, curiosity, survival...  
  
Cyclonus thought this had to be a new one: running out of condoms.  
  
It was his fault. He though he had plenty of condoms at his apartment, but he didn't realize that the extra bulk at the bottom that he thought were more were actually papers with coupons and such for more of the brand. Damn it, he should have known.  
  
Now on a perfect Saturday night with Tailgate more than ready for a long night of his work, he had suddenly realized they were down to two condoms. He may have been able to hold it off for longer than most men, but even he couldn't get through a night on just two condoms.  
  
Surprisingly, it had been Tailgate who had made the suggestion of him using her second entrance. They had been in the middle of trying to figure out how to make due with two condoms when she suggested it. She had just taken a shower before this, so it was relatively clean and there were no fears of getting pregnant with sperm up her rectum, so it made sense.  
  
Trouble was that Cyclonus had only done little prep work with her anal entrance since their relationship started not long ago. Other than some fingers and a very small toy once for an interesting attempt at double penetration, she hadn't really been stretched back there.  
  
But Tailgate had convinced him otherwise. Little did he know at this point that Tailgate, who was under the impression that Cyclonus was only with her for the sex and not that they were in a relationship as the latter thought, was worried what would happen if she never did it back there. The fear of losing him was too much for her and becoming boring and not pleasing him along with the other prominent fear of him leaving her if she were to become pregnant was enough for her to want to do this. To make him happy, keep him sated, and otherwise lower her still-high chances of a little bun being baked in the oven.  
  
So after several orgasms for Tailgate and two for Cyclonus, it was time for the moment of truth. After using his fingers and a few toys to get her off, he used his fingers to stretch her more before lubing a small, but longer toy to put inside her. After she became use to it while he fingered her off, he proceeded to have her ride him as he got off his first orgasm, the toy snug in her anal entrance while her vaginal entrance was becoming more and more wet with more of her fluids.  
  
The second round was about the same, only he put a smaller, but wider toy into her. It took a few kisses and some rubbing of her clitoris to help her get it in, but after he secured it inside her, he took to licking her off before taking her again. He may have also pumped the toy into her second entrance while taking her, but he couldn't help how tight she became when the toy went deeper into her by his administrations.  
  
And now after his second orgasm was where they were at.  
  
Cyclonus gently swiveled the toy out of her aching hole, the lube accentuating the gaping hole as it shrunk back to its normal size. Throwing it off the bed next to the other toy, he applied more lube to the entrance slowly as he heard her wince. "Are you sure about this Tailgate?"  
  
His lover grimaced a little as the cold lube touched her backside. Primus, this was going to take some getting used to. That is, if she got over the pain. "I-I'm fine, just..."  
  
"Nervous?" He couldn't help it; he could see she was shaking.  
  
"...Just jitters...I-It's my first time with...y-you back there."  
  
"Don't worry. I'm going to be careful. But just remember you can tell me to stop if you feel something's wrong-"  
  
"I-I know, I know," Primus, did Tailgate know. But she's didn't know if she could. Some of her friends had told her about their bad experiences with anal sex. Especially how painful it could be with improper prepping. But Cyclonus...he wouldn't be doing all this unless it was to make her feel good. He had told her before that he only had a good time when she did.  
  
She was still scared shitless when Cyclonus moved to lay her down as he crawled over her.  
  
"C-Cyc-!"  
  
He silenced her with a kiss, probably to distract her as she felt him moving below... only to gasp and groan into the kiss as his bare half-hard cock entered her wet pussy.  
  
The normally stoic man was almost undone by the clamp of her welcoming body. Primus, it had been so long since he had felt the bare muscle of a woman's vagina tight around his hard mushroom head. And Tailgate, Primus, he almost wanted to just throw it to the wind and stay inside her womanhood like this for the rest of the night.  
  
But he knew he couldn't. He had promised to take her in her second entrance. He had put her through enough to get her properly stretched for this. And to just not do it and put his seed into her womb... No, he would never do that to her. He could not just forsake her safety and future just so he could have a good fuck. It would end her career if she got pregnant and someone were to find out it was because of him. Hell, he had started to not care about his own consequences for this relationship, rather only thinking of what could happen to her. He had no idea how he would take all the blame and leave her with her job and as much dignity as he could, but he would think of something somehow.  
  
A loud moan snapped him out of his thoughts. Finding himself over the woman he loved, Cyclonus remembered where he was exactly and controlled himself enough to give another hard thrust before pulling out.  
  
Tailgate responded with a sad coo, missing his warmth filling her up.  
  
"Are you still okay with this?"  
  
She hesitated for a moment before giving a quick nod as she closed her eyes.  
  
He didn't give with just that. "Tailgate," he moved his clean hand up to caress her cheek, causing her to open her eyes to stare at his again, "Please... tell me if you want to do this. I'll be fine if you say you don't want to. There are other ways we can both enjoy each other that won't require me just putting my penis inside of you."  
  
She chuckled slightly. Primus, Cyclonus could just sound so funny when he was talking so seriously with how proper his words were. But the look on his face... she blushed and looked away.  
  
He didn't let her stay that way for long. "Tailgate?"  
  
"Will..." she started slowly, "Will you... be... gentle?"  
  
Tailgate though she swooned when he gave her a small smile before he kissed her again. "I will. For you, I will."  
  
Pulling back, Cyclonus pressed the head of his manhood to her anal entrance. Tailgate couldn't help but to jump at the touch. Primus, she forgot he was big! He was much more than the toys he had used before.  
  
His hands came up to hold her. "You must be as still as you can. I just need to push my head through and then it'll be easier to do the rest. But you must try to be as still as you can or else I could hurt you by accident."  
  
Now even more scared, Tailgate was barely able to nod as Cyclonus pulled her into a tight hug. "I'm going to push in. One moment of pain. Your entrance will fight the intrusion and it will not accept the stretching first thing. Once I get my head in, your body will try to push. Don't. Just breath, relax your bottom, and let your body get used to me. Understood."  
  
She nodded again as she held him tight.  
  
And true to what he said, there was pain. It was like something hot was trying to rip her in two. Her broken virginity had been a bit sore at first, but it was nothing like this! But his hand gripping her back brought her to remember to breath, letting the intrusion push inside past her tight, anal ring.  
  
"Breath. I'll go when you're ready. I can pull out if you wish."  
  
Her breaths hitched repeatedly as she struggled to take deep breaths. Primus, the closest she could think for this feeling was to only push. That was what the body was supposed to do in this scenario, but it wasn't what she was trying to do. It wasn't her trying to expel, she was trying to intake Cyclonus's cock. It just wasn't like her pussy at all!  
  
But to her relief, after several minutes, the pain and ache went away mostly as a new feeling emerged. It wasn't so much pleasure as it was... unique. And quite inviting, as she suddenly tightened her thigh muscles to try to pull him in further.  
  
Cyclonus panted as she tightened around him. “Do you want me to push in further?”  
  
Now struggling to breathe herself, Tailgate managed to turn her head enough to nod. She unconsciously squeezed her buttock’s muscles again.  
  
As the tightness of her anal entrance aroused him even further, he had no choice but to let them pull him in deeper. Though not as wet and inviting as her vagina, Tailgate’s back entrance was tight. It squeezed him in different ways than her other hole had and with the lube, it just slid further and further into her.  
  
Tailgate continued to grunt and shuffle as Cyclonus’s penis pressed on. He was big. Bigger than his fingers and most definitely bigger than the toys. She couldn’t understand how he could fit everything back there, but it was getting close. Really close. She was certain he was about to finish pushing in soon, but to haven’t hit the end yet…  
  
She could feel Cyclonus slump over just as he bottomed out. Primus, she was unaware of how deep he was, but she could definitely feel the stretch. It wasn't just her anal entrance, it was just her whole... well, the rest of where that hole lead to.  
  
Heavy breathing filled her ears as she looked up, seeing him shutting his eyes tight as his arms shook. "Cy-Cylonus?"  
  
"Just... give me a moment. I don't want to do something I'll regret."  
  
Water gathered in the corners of her eyes as he breathed deep breaths in and out, his body literally shaking as though he were hurt. That wasn't... she couldn't have possibly hurt him, could she?  
  
"Cyclonus? A-Are you okay?"  
  
He opened up one eye as his breathing still labored. "I-I'm fine. J-Just tight... you're so tight... around me... feels good."  
  
"I-I-?"  
  
"But I don't want to do something that will hurt you. I want you to be comfortable and stretched enough with me inside you before I let go. Just please..."  
  
Nodding in agreement, Tailgate soon began to breathe in time with his breathing. The hard object inside of her started to make her feel good... well, at least not so uncomfortable. It was hot and burning inside of her, but she could see where the pleasure came from this. She swallowed and accidentally wiggled her hips a bit, causing Cyclonus to move as they both gasped out.   
  
"Sh-! I didn't mean to-!"  
  
"N-No! ... I-I mean... no... i-it's okay now."  
  
He finally opened his eyes with what appeared to be shock coursing through them. He looked at her, almost looking through her, she thought.  
  
"Tailgate... are you sure?"  
  
"I-It's not painful now," she swallowed, "I-I think I'm ready."  
  
"You certain?"  
  
"...Y-Yes."  
  
He took one last hard look at her before he heaved, taking in another deep breath before he slowly started to pull out again.  
  
Primus, it was rough for them both. Cyclonus had to hold back the urge to pull out quickly and shove it back in. Tailgate was trying to not push, even though he was pulling out of her. It was just so weird.  
  
Finally most of the way out, the taller one breathed out the breath he had been holding in. Watching her face for any pain, he slowly pushed back in again. Other than a gasp from his lover, it was not as hard as before as he was able to push back in with less resistance than before. Before he knew it, he had bottomed out and was pulling out again.  
  
Tailgate was doing her best to not show any signs of discomfort on her face. Her hands were clawing into the sheets (she was glad she had cut them recently) and it just felt so weird. She had no idea what to do other than follow Cyclonus's advice. It was pleasurable, but the weirdness was just too much.  
  
Suddenly, she felt something at her neglected clit. She spasmed back, her back arching as his fingers began to play with her.  
  
"C-C-Cy-!" Tailgate could barely get a word out as she soon began to buck with his thrusts, which were not starting to speed up, "M-More! Oh Primus, I need-!"  
  
Cyclonus didn't disappoint as he moved his hand to wrap her legs tighter around him before moving a hand up to squeeze at her breast. All while he was still thrusting into her.  
  
It was a few minutes later that she finally orgasmed. Cyclonus stopped, still having not had his yet, as he waited for her to recover. "Do you still want to continue?"  
  
Tailgate closed her eyes as she steadied her breath. Primus, this was going to take a lot of getting used to. If she ever got used to it, that was.  
  
"Tailgate?"  
  
She opened her eyes to look at her lover. It was rough, but she didn't care. As long as Cyclonus stayed with her, she could handle it. She would be willing to put up with it as long as it kept him happy.  
  
Smiling softly, she pulled him down for a quick kiss before she finally spoke, "I-I'm ready... p-please continue."  
  
And as he kissed her back and continued, she felt happy. And as he released inside of her, she felt so much pleasure with his and her own third orgasm. And as he snuggled up with her later after more rounds, she felt loved.  
  
For all she needed was Cyclonus.


End file.
